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07-SEPTEMBER-2008 03:17:44 - Atomoxetine Atomoxetine Systematic IUPAC name 3R-N-methyl-3-2-methylphenoxy-3-phenyl-propan-1-amine Identifiers CAS number 83015-26-3 ATC code N06BA09 PubChem 54841 DrugBank APRD00614 Chemical data Formula C17H21NO Mol. mass 255.355 g/mol 291.820 g/mol hydrochloride SMILES eMolecules PubChem Pharmacokinetic data Bioavailability 63 to 94% Protein binding 40% Metabolism Hepatic, via CYP2D6 Half life 5 hours Excretion Renal 80% and fecal 17% Therapeutic considerations Pregnancy cat. B3AU CUS Legal status POMUK Unscheduled U.S. Routes Oral Capsules: 10, 18, 25, 40, and 60 mg; in some countries 80 and 100 mg are also available Eli Lilly's Strattera capsules. Eli Lilly's Strattera capsules. Atomoxetine is a non-stimulant drug approved for the treatment of attention-deficit hyperactivity disorder ADHD. It is sold in the form of the hydrochloride salt of atomoxetine. This chemical is manufactured and marketed under the brand name Strattera by Eli Lilly and Company and as a generic Tomoxetin by Torrent Pharmaceuticals. There is currently no generic available within the United States due to patent restrictions. Contents 1 Use 2 Nomenclature 3 Chemistry and composition 4 Side effects 4.1 Discontinuation adverse effects 4.2 Psychiatric reactions 5 Potential for abuse 6 Off-label uses 7 Experimental uses 8 References 9 External links Use This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. August 2008 Classified as a norepinephrine noradrenaline reuptake inhibitor, atomoxetine is approved for use in children, adolescents, and adults. However, its efficacy has not been studied in children under six years old. Its advantage over stimulants for the treatment of ADHD is that it has less abuse potential than stimulants, is not scheduled as a controlled substance and has proven in clinical trials to offer 24 hour coverage of symptoms associated with ADHD in adults and children. Although the drug can be felt right away, it does not start working properly for 3-4 weeks time. Users should expect to feel tired and groggy for a few weeks. Eventually, the system adapts to the drug and the benefits can be felt. Users are recommended to continue taking the drug for at least three weeks before deciding to discontinue its use. Strattera was originally intended to be a new antidepressant drug; however, in clinical trials, no such benefits could be proven. Since norepinephrine is believed to play a role in ADHD, Strattera was tested-and subsequently approved-as an ADHD treatment. Though approved for ADHD, many doctors prescribe it off-label as an anti-psychotic in cases of certain disorders of thought and less serious mental problems, such as dyslexia, clumsiness, and schizoaffective disorder. This is due to its help in 'calming down' and steadying of thought processes, improving symptoms associated with less serious types and degrees of schizophrenia. In this case, atomoxetine has great potential in the treatment of schizophrenia and the Predominantly Inattentive subtype of ADHD once separately designated 'Attention-Deficit Disorder'. In many cases of the above-mentioned disorders of thought, it is said to work seamlessly better and with less negative side-effects than any of the available approved anti-psychotics. Nomenclature Atomoxetine was originally known as tomoxetine. However, the U.S. Food and Drug Administration FDA requested the name be changed because, in their opinion, the similarity of tomoxetine to tamoxifen a breast cancer drug could lead to dispensing errors at pharmacies. Chemistry and composition Atomoxetine is designated chemically as --N-methyl-3-phenyl-3-o-tolyloxy-propylamine hydrochloride, and has a molecular mass of 291.82. It has a solubility of 27.8 mg/mL in water. Atomoxetine is a white solid that exists as a granular powder inside the capsule, along with pre-gelatinized starch and dimethicone. The capsule shells contain gelatin, sodium lauryl sulfate, FDC Blue No. 2, synthetic yellow iron oxide, titanium dioxide, red iron oxide, edible black ink, and trace amounts of other inactive ingredients. Side effects This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. June 2008 The most common side effects in children, adolescents, and adults are upset stomach, sporadic nausea, and sudden vomiting. The medication's tendency to decrease appetite may contribute to this problem, as taking Strattera on an empty stomach is usually discouraged; it can also be a problem in itself, in the form of hunger pangs. Consumption of dairy products can cause further upset. A significant minority of adult male patients taking Strattera suffer minor to severe sexual side effects, including erectile dysfunction, retrograde ejaculation, painful orgasm, and the decoupling of orgasm from ejaculation, wherein ejaculation takes place up to ten seconds before or after orgasm. Occasionally after prolonged use some teenagers have experienced slow onset mild depression while using Stratteracitation needed Two confirmed cases of liver injury have been reported by Eli Lilly and Company out of approximately two million prescriptions written. In both cases upon discontinuation of atomoxetine, patients' liver functions returned to normal. Discontinuation adverse effects Further information: Chemical synapse The central nervous system CNS adapts to the presence of psychoactive drugs. Such adaptation commonly involves the readjustment of neuroreceptors to compensate for the acute pharmacological action of the medication. This adaptation theory also explains why withdrawal symptoms and signs can occur on the discontinuation of such medications as clearance of drug can occur at a rate faster than the brain can readjust to the absence of medication. Hence, pharmacodynamic and pharmacokinetic factors contribute to the risk of a withdrawal syndrome. Psychiatric reactions In September 2005, Strattera was determined to increase risk of suicidal thoughts among children and adolescents; one attempted suicide and five cases of suicidal thoughts were reported out of 1,357 young patients taking Strattera, while none was reported out of a control group of 851 taking placebos. 1, 2. The FDA has required that black box warnings be placed on all antidepressant medications warning they may result in increased risk of suicidal tendencies in children and adolescents; therefore, Strattera bears such a warning. In less than three years on the market 10,988 adverse psychiatric reactions have been reported to Eli Lilly for the ADHD drug Strattera, according to the British Medicines and Healthcare products Regulatory Agency MHRA, January 2006. Potential for abuse To date, the potential for abuse of Strattera has not been exhaustively researched. The two studies that have been performed suggest that atomoxetine has a low to moderate risk for abuse, since it has a long titration time meaning that it may have no effect on the user unless they've been taking it regularly for days and does not produce strong stimulating effects like most other ADHD medications which are usually dopamine reuptake inhibitors. Monkeys will not self-administer atomoxetine at the doses tested Gasior et al, Neuropharm 30:758, 2005; Wee Woolverton, Drug Alcohol Depend 75:271, 2004. However, rats, pigeons and monkeys trained to distinguish cocaine or methamphetamine from saline indicate that atomoxetine produces effects indistinguishable from low doses of cocaine or methamphetamine, but not at all like high doses of cocaine Spealman, JPET 271:53, 1995; Sasaki et al., Psychopharm 120:303, 1995. No place preference studies have been conducted with atomoxetine. It may be abused if taken in larger amounts than the daily dosage, the effects may be compared to those experienced on amphetamines that are also used for ADHD medication. Off-label uses While depression is most commonly associated with the neurotransmitter serotonin, an imbalance of other neurotransmitters may also result in clinical depression. To that end, atomoxetine, which inhibits the reuptake of norepinephrine, was originally explored by Eli Lilly as a treatment for depression, but did not show a benefit to risk ratio in trials. Failed clinical trials are not submitted to drug regulatory agencies and are considered trade secrets. Subsequently, Lilly then chose to pursue an ADHD treatment route for atomoxetine. Many patients have seen a pronounced anti-depressive effect in conjunction with other antidepressants. More study is needed to understand the full pharmacodynamics.1234 Experimental uses A small 40 people, 10-week, double-blind clinical trial was reported in the Journal of Clinical Psychiatry on the effectiveness of atomoxetine for treating binge eating disorder. The results of the trial was that atomoxetine was associated with a significantly greater rate of reduction in binge-eating episode frequency, weight, and body mass index. The average daily dose given was 106 mg/day. The authors concluded that atomoxetine is effective for short term treatment of binge eating disorder.5 A preliminary 12-week, randomized, double-blind, placebo-controlled trial was conducted at Duke University Medical Center which studied the effectiveness of atomoxetine on adult obese women. The study included 30 obese women with an average body mass index of 36.1. Fifteen women were given atomoxetine therapy starting at 25 mg/day with a gradual increase to 100 mg/day over 1 week. Fifteen women were given a placebo with identical dosing. By the end of the trial, the atomoxetine group lost an average of 3.6 kg 3.7% of their body mass vs a 0.1 kg gain in the placebo group 0.2% gain. Three participants in the atomoxetine group and none in the placebo group lost greater than 5% of their mass.6 References ^ Biederman J, Spencer TJ March, 2006. Atomoxetine and adult attention-deficit/hyperactivity disorder: the effects of comorbidity. ^ Adli M, Pilhatsch MK March, 2006. Augmentation with atomoxetine in treatment-resistant depression with psychotic features. A case report. Pharmacopsychiatry 39: 79. doi:10.1055/s-2006-931547. ^ Price LH, Carpenter LL Oct, 2005. Augmentation with open-label atomoxetine for partial or nonresponse to antidepressants. ^ Biederman, J, Kratochvil CJ Sept, 2005. Atomoxetine alone or combined with fluoxetine for treating ADHD with comorbid depressive or anxiety symptoms. ^ McElroy, Susan 2007, Atomoxetine in the Treatment of Binge-Eating Disorder: A Randomized Placebo-Controlled Trial, Journal of Clinical Psychiatry 683: 390-398, PMID 17388708, http://www.psychiatrist.com.prxy3.ursus.maine.edu/privatepdf/2007/v68n03/v68n0306.pdf ^ Gadde, K.M. July 2006, Atomoxetine for weight reduction in obese women: a preliminary randomised controlled trial, International Journal of Obesity 307: 1138-1142, doi:10.1038/sj.ijo.0803223, PMID 16418753 External links RxList.com - Strattera Strattera Available Dosages Detailed Strattera Consumer Information: Uses, Precautions, Side Effects All Lilly trials MSDS for Atomoxetine HCl Strattera Related Published Studies By learning from failures, Lilly keeps drug pipeline full, The Wall Street Journal, April 21, 2004 v d e Psychoanaleptics: antidepressants N06A MAOIs Clorgiline Iproclozide Iproniazid Isocarboxazid Minaprine Nialamide Pargyline Phenelzine Toloxatone Tranylcypromine MAOB: Rasagiline Selegiline RIMAs: Befloxatone Brofaromine Cimoxatone Beta-carbolines Harmaline Moclobemide RIs S RI SS RI Alaproclate, Citalopram, Dapoxetine, Escitalopram, Femoxetine, Fluoxetine, Fluvoxamine, Paroxetine, Sertraline, Zimelidine TCAs/Tetras Cianopramine, Clomipramine, Nefazodone, Trazodone N RI / A RI Atomoxetine Ciclazindol Maprotiline Nisoxetine Oxaprotiline Reboxetine Talopram Viloxazine TCAs/Tetras Amitriptyline, Amoxapine, Butriptyline, Desipramine/Lofepramine, Dibenzepin, Dosulepin, Doxepin, Imipramine, Iprindole, Melitracen, Nitroxazepine, Nortriptyline, Protriptyline, Trimipramine D RI Medifoxamine Phenmetrazine Vanoxerine TCAs Amineptine SN RI Bicifadine Clovoxamine Desvenlafaxine Duloxetine Milnacipran Nefazodone Venlafaxine ND RI Bupropion Nomifensine SND RI Brasofensine Diclofensine Tesofensine SSREs Tianeptine AAs Tetras Mianserin, Mirtazapine v d e Psychoanaleptics: psychostimulants, agents used for ADHD and nootropics N06B Centrally acting sympathomimetics Amphetamine - Amphetaminil - Atomoxetine - Dextroamphetamine - Dextromethamphetamine - Fencamfamin - Fenozolone - Fenetylline - Methylphenidate - Mesocarb - Pemoline - Pipradrol - Prolintane Xanthine derivatives Caffeine - Propentofylline Glutamate receptor Racetams Aniracetam - Nefiracetam - Oxiracetam - Phenylpiracetam - Piracetam - Pramiracetam Ampakines CX-516 - CX-546 - CX-614 - CX-691 - CX-717 - IDRA-21 - LY-503,430 - PEPA Eugeroics / Benzhydryl compounds Adrafinil - Armodafinil - Modafinil Histamine H3 receptor antagonists ABT-239 - Ciproxifan Other psychostimulants and nootropics Acetylcarnitine - Citicoline - Cyprodenate - Idebenone - Ispronicline - Deanol - Dimebon - Fipexide - Linopirdine - Meclofenoxate - Nizofenone - Pirisudanol - Pyritinol - Sulbutiamine - Taltirelin - Tricyanoaminopropene - Vinpocetine Retrieved from http://en..org/wiki/Atomoxetine Categories: Norepinephrine reuptake inhibitors | Eli Lilly and CompanyHidden categories: Articles needing additional references from August 2008 | Articles needing additional references from June 2008 | All articles with statements | Articles with statements since October 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Nederlands Norsk bokmål Polski Português This page was last modified on 27 August 2008, at 02:35
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